His paternal grandfather, Louis Ehrlich, was born in Chisinäu in 1901. In 2005, the World Economic Forum named Stephens a Young Global Leader. He won the 2008 Eric Breindel Award for Excellence in Opinion Journalism. In 2009, he was named deputy editorial page editor after Melanie Kirkpatrick's retirement. In 2010, Stephens won the Reason Foundation's Bastiat Prize. Stephens won the 2013 Pulitzer Prize for Commentary for "his incisive columns on American foreign policy and domestic politics, often enlivened by a contrarian twist". He is a national judge of the Livingston Award. In 2015, Stephens joined the Real-Time Academy of Short Form Arts & Sciences. The Real-Time Academy judges contestants for the Shorty Awards, which honor the best individuals and organizations on social media. Stephens has chaired two Pulitzer juries. In 2016, he chaired the one that awarded the Pulitzer Prize for International Reporting to Alyssa Rubin of The New York Times. In 2017, Stephens chaired the jury that awarded the Pulitzer Prize for Editorial Writing to Art Cullen of The Storm Lake Times. In 2002, Stephens moved to Israel to become the editor-in-chief of The Jerusalem Post. Stephens left 'The Jerusalem Post in 2004 and returned to The Wall Street Journal. In 2017, Stephens left the Wall Street Journal, joined The New York 'Times as an opinion columnist, and on-air contributor to NBC News and MSNBC.